4-(2-Chloroethylamino)-1-methylpiperidine dihydrochloride

ABSTRACT

The title compound is an anthelmintic agent.

United States Patent 1 Schwan [4 1 May '13, 19754-(2-CHLOROETHYLAMINO)-l- OTHER PUBLICATIONS METHYLPIPERIDINEDIHYDROCHLORIDE [76] Inventor: Thomas J. Schwan, 8 Hillview Dr.,Hohenlohe-Oehringen etaL, MonatshoChem. 96 (l),

Norwich, NY. 13815 246-256 (1965).

' [22 Filed: Jan. 25, 1974 [2]] Appl. No.: 436,460 Primary Examiner-G.Thomas Todd 52 U.S. c1 260/293.87; 424/267 [51] Int. CL; C07d 29/28 57ABSTRACT [58] Field of Search 260/293.87 I

The title compound is an anthelmintic agent. [56] References Cited '1Claim, No Drawings 4-(2-CHLOROETHYLAMINO)-l- METHYLPIPERIDINEDIHYDROCHLORIDE This invention is concerned with the compound 4-( 2-chloroethylamino)- l -methylpiperidine dihydrochloride. It is ananthelmintic agent. For example, when administered in a dose of about300 mg/kg by gavage in an aqueous suspension to mice harboring Ascarissuum worms, it effects greater than 50 percent eradication of the wormpopulation.

In order that this invention may be readily available to and understoodby those skilled in the art, the now preferred method for itspreparation is set forth:

To a cooled solution of 63.0 g (0.40 mole) of4-(2-hydroxyethylamino)-l-methylpiperidine in 750 ml chloroform wasadded slowly with vigorous stirring 58.1 ml (95.2 g, 0.80 mole) ofthionyl chloride. The

mixture was stirred and refluxed for 3 hours and cooled. After thesolvents were removed in vacuo the residue was taken up in 700 ml hotmethanol. The solution was cooled and ml methanol saturated withhydrogen chloride was added. Upon cooling there was obtained in twocrops 58 g (58 percent) of the product, m.p. 264-268. The analyticalsample, m.p. 267269, was obtained by recrystallization from absoluteethanol.

Anal. Calcd. for C H C1N .2HCl: C, 38.49; H, 7.67;

Cl, 42.61; N, 11.23

Found: C, 38.57; H, 7.85; Cl, 42.57; N, 11.28.

What is claimed is:

l. 4-(2-Chloroethylamino)-l-methylpiperidine dihydrochloride.

1. 4-(2-CHLORETHYLAMINO)-1-METHYLPIPERIDINE DIHYDROCHLORIDE.